Acid-catalyzed Dimerization Reaction of Pyrroles to Synthesize Hexaaryl-4,8-dihydropyrrolo[2,3-f]indoles

doi:10.1007/s40242-018-8031-3

Chemical Research in Chinese Universities ›› 2018, Vol. 34 ›› Issue (4): 559-563.doi: 10.1007/s40242-018-8031-3

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Acid-catalyzed Dimerization Reaction of Pyrroles to Synthesize Hexaaryl-4,8-dihydropyrrolo[2,3-f]indoles

ZHANG Shuai, ZHENG Ziqi, ZHANG Tong, FU Xue, SHI Shaojia, JIANG Lin, YIN Hongzong

College of Chemistry and Material Science, Shandong Agricultural University, Taian 271018, P. R. China

Received:2018-01-25 Online:2018-08-01 Published:2018-04-16
Contact: ZHANG Shuai, YIN Hongzong E-mail:hyzs@sdau.edu.cn;hzyin@sdau.edu.cn
Supported by:
Supported by the Natural Science Foundation of Shandong Province, China(No.ZR2017BB025), the University Science and Technology Program of Shandong Province, China(No.J16LC15) and the Youth Science and Technology Innovation Fund of Shandong Agricultural University, China(No.24166).

Abstract

Abstract: Pyrroloindoles, as a kind of promising small-melecular hole injetion materials, have attracted wide attention. Herein, we described a simple metal-free method for the synthesis of 4,8-dihydropyrrolo[2,3-f]indole compounds through the acid-catalyzed dimerization reaction of pyrroles. The structures of target 4,8-dihydropyrrolo-[2,3-f]indoles were confirmed by NMR spectrum and X-ray single crystal diffraction. Notably, pyrrole substrates were synthesized conveniently starting from available biological dipeptides. cis-Configuration was preferred when bulky p-toluene sulfonic acid(TsOH) was employed. Excessive aicds empoyed in dimerization would lead to the formation of quantitative pyrrolium chloride intermediate, restraining further conversion to target compounds. Furthermore, the dimerization process was monitored by ¹H NMR spectrum, proving that it followed a second-order kinetics, providing significant insight to the mechanism of dimerization reaction.

Key words: Dimerazation, Pyrroloindole, Benzoheterole, Pyrrole

ZHANG Shuai, ZHENG Ziqi, ZHANG Tong, FU Xue, SHI Shaojia, JIANG Lin, YIN Hongzong. Acid-catalyzed Dimerization Reaction of Pyrroles to Synthesize Hexaaryl-4,8-dihydropyrrolo[2,3-f]indoles[J]. Chemical Research in Chinese Universities, 2018, 34(4): 559-563.

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Acid-catalyzed Dimerization Reaction of Pyrroles to Synthesize Hexaaryl-4,8-dihydropyrrolo[2,3-f]indoles

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